HCID 15463464, compound → HCID 54430701, compound

HRID 2256473Notes

Reaction equation

HRID 2256473 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:26])([CH2:18][O:19]C(=O)CCCC)[CH2:10][O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]>C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:26])([CH2:10][O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:18][OH:19]

Participants

3

Reactant 1

HCID 15463464HCID 15463464, compound

Product 1

HCID 54430701HCID 54430701, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 175AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A 200 ml reaction vessel was charged with 2 g of 2-(2,4-difluorophenyl)-1,3-di-n-pentanoyloxy-2-propanol, 100 mg of Lipase D made by Amano Pharmaceutical Co., Ltd. (derived from Rhizopus delemer, Enzyme No. 6) and 100 ml of 50 mM acetate buffer (pH 5). The resulting mixture was stirred at 30° C. to react for 18 hours. After the reaction liquid was extracted three times with 50 ml of ethyl acetate, the organic layers were combined and the combined organic layer was washed with saturated aqueous solution with sodium bicarbonate and with saturated aqueous solution with sodium chloride and further dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2) to give 1.01 g of oily (R)-2-(2,4-difluorophenyl)-3-n-pentanoyloxy-1,2-propanediol. An optical purity thereof was determined in the same manner as Example 35. (Elution time: 13.7 minutes ((R)-form) and 11.1 minutes ((S)-form)).

Workup

  1. customA 200 ml reaction vessel
  2. customto react for 18 hours
  3. customAfter the reaction liquid
  4. extractionwas extracted three times with 50 ml of ethyl acetate
  5. washthe combined organic layer was washed with saturated aqueous solution with sodium bicarbonate and with saturated aqueous solution with sodium chloride
  6. dry with materialfurther dried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-a8cbaa0a8e284c83a511c899b5900b6c
Source dataset
uspto-grants-1997_08
Patent number
US05654472

Reaction notes

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